Thermal transformations of 2H-benzimidazole 1,3-dioxides Full article
| Journal |
Russian Chemical Bulletin
ISSN: 1066-5285 , E-ISSN: 1573-9171 |
||
|---|---|---|---|
| Output data | Year: 2011, Volume: 60, Number: 8, Pages: 1723-1728 Pages count : DOI: 10.1007/s11172-011-0257-x | ||
| Tags | 2H-benzimidazoles; 2,1,4-benzoxadiazines; heterocyclic N-oxides; rearrangements; phototransformation; oxidation | ||
| Authors |
|
||
| Affiliations |
|
Abstract:
Thermal transformations of 2H-benzimidazole 1,3-dioxides represented by spiro[2H-benz-imidazole-2,1'-cyclohexane] 1,3-dioxide and its 5-nitro derivative were studied. Their heating resulted in reversible isomerization to spiro[3H-[2,1,4]benzoxadiazine-3,1'-cyclohexane] 4-oxides. More prolonged heating of 2H-benzimidazole 1,3-dioxides caused sequential elimination of the first and then (at higher temperature) the second N-oxide oxygen atom to form 2H-benzimidazole derivatives, which upon further heating were transformed to 7,8,9,10-tetrahydro-6H-azepino[1,2-a]benzimidazoles. A scheme of the process was suggested, which described the experimental data obtained. Spiro[3H-[2,1,4]benzoxadiazine-3,1'-cyclohexane] 4-oxides on exposure to the sunlight were quantitatively transformed to 2H-benzimidazole 1,3-dioxides.
Cite:
Samsonov V.A.
, Bagryanskaya I.Y.
, Gatilov Y.V.
, Savel'ev V.A.
Thermal transformations of 2H-benzimidazole 1,3-dioxides
Russian Chemical Bulletin. 2011. V.60. N8. P.1723-1728. DOI: 10.1007/s11172-011-0257-x WOS Scopus РИНЦ OpenAlex
Thermal transformations of 2H-benzimidazole 1,3-dioxides
Russian Chemical Bulletin. 2011. V.60. N8. P.1723-1728. DOI: 10.1007/s11172-011-0257-x WOS Scopus РИНЦ OpenAlex
Dates:
| Published print: | Aug 1, 2011 |
| Published online: | May 29, 2012 |
Identifiers:
| Web of science: | WOS:000304617900032 |
| Scopus: | 2-s2.0-84864546127 |
| Elibrary: | 20523810 |
| OpenAlex: | W2088612296 |